Off Season Travel

So, you haven’t cashed in your vacay days yet – and summer Fridays meant leaving work at 8 instead of 9. But all those unused days now means you can cash in when it really counts – the off-season. You’re used to closing deals; now let the deals come to you.

The good news: It’s always off-season somewhere. Tuscany in October, Cannes in December, and St. Barth’s in May. No, you won’t see Bon Jovi and his feathered locks on the beach but you also won’t be shelling out $15K a night for the chance to rub elbows with the rich and famous. Listening to “Livin’ on a Prayer” while drinking a flute – or a bottle – of Dom should be more than enough to make up for it. If not, just take a swim in the pile of money you saved.

Without the Royal Pains: The Hamptons

Optimal Off-Season: October through New Year’s Eve, and May–June

Why: In the off-season, you don’t need a Learjet to avoid the summer traffic. Even for us mere mortals, it’s clear sailing on the Long Island Expressway. While nothing beats the summer debauchery of the Hamptons, with its pop-up clubs and restaurants, it sure is nice to hear these three words: No reservations necessary. But in the end, as glamorous as the Hamptons sound, they’re really just a string of chilled-out beach towns.

To Do: Hamptons International Film Festival, Nick & Toni’s with no wait, and wine-tasting at Channing Daughters and Wolffer Estates. Also, for the record, pumpkin patches are not just for kids, especially with warm apple cider and farmers markets. If you’re lucky and it’s an Indian Summer, you can park at the beach on a weekend sans beach pass. October waters can be even warmer than August.

Such a Deal: The hotels have milked what they can from the weekenders, and October is when the deals really kick in. Check in at the Inn at Windmill Lane for $575, regularly $800. Or, bed down at c/o the Maidstone where during the week, you get two nights for the price of one. For a full weekend escape: Homes that normally rent for $25K/month go for a fraction of that from now until the summer season begins in May.

Livin’ on a Prayer in St. Barth’s

Optimal Off-Season: October–November, April–July

Why: No, you won’t see Bon Jovi, but you also won’t be shelling out big bucks to mingle with celebs. And let’s face it, their handlers wouldn’t let you talk to them anyway. Listening to “Livin’ on a Prayer” while drinking a flute – or a bottle – of Dom should be more than enough to make up for it.

To Do: Exactly what you would do in high season, but at a 30 percent discount. There is a reason that St. Barth’s is the playground of the moneyed – long white-sand beaches, gorgeous accommodation, and the best food in the Caribbean. The truffle spaghetti at Le Toiny is reason enough to fly to St. Barth’s for the weekend. This isn’t your typical Caribbean getaway; it’s far more cultured and, barring Mustique, the service is unrivaled in the region. St. Barth’s is more St. Tropez, but without the cranky French.

Such a Deal: Le Sereno is one of the best values for luxury in St. Barth’s, and even more so in low-season. Rooms start around $550, versus $730 in high season. Catch them at the right time, and you may be able to score packages that include spa treatments and dinner in their gourmet waterfront restaurant. St. Barth’s is not an inexpensive place, but those who save their pennies for a sunny day can get a glimpse of how the other half lives.

Under the Tuscan Fall Sun

Optimal Off-Season: October–November, April–May

Why: The amateurs who travel like the Griswalds in National Lampoon’s European Vacation are long gone, and flight prices and hotel rates are gentler on the pocket. Real insiders know that the fall in Tuscany is the best time of year to visit. And hello, truffle season.

To Do: Shop for a bolt of Loro Piana cashmere, which you can only buy in Florence; rent that villa in Tuscany; eat your face off with pasta; and catch the vintners harvesting grapes and celebrate the fruit of their labors with leisurely wine dinners.

Such a Deal: With exchange rates finally in favor of the U.S. dollar, Europe is affordable again for Americans. Hotels are doing their part. The Four Seasons Florence is offering four nights for the price of three, where you’ll be living like the Medicis. Literally. The Four Seasons is housed in the Medici family’s former palace. Within Tuscany, Castiglion del Bosco has rates at over 40 percent off summer high season. And, the normally you-can’t-touch-this Borgo Finocchieto features a slightly lower rate than the usual $10K/night for the nine-room manor home.

Yes, You Cannes

Optimal Off-Season: October–December

Why: It’s confirmed: The rosé in Cannes tastes almost as good in the off-season as it does in July. And better yet, it is still possible to dance on a table after imbibing too much of it. As a city of business as much as tourism, Cannes thrives year-round. With its mild weather, you may not be in a string bikini in the middle of December, but you can easily spend an afternoon lolling on the beach.

To Do: Le Baoli on La Croisette, where there is just slightly less attitude in the fall months, lunch at Le Martinique’s beach club, and people-watching at the Carlton. Cannes has a great restaurant scene frequented by locals throughout the year, from the traditional French brasserie Pastis to Casa Mia, an Italian restaurant that seems more New York than Cannes.

Such a Deal: Classic rooms at the Carlton dip as low as 200 euro a night in December, before the New Year’s Eve festivities, whereas in high season, these same rooms top 700 euro.